Diisopropylethylamine → HCID 68602346, compound

HRID 714485Notes

Reaction equation

HRID 714485 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16](O)=[O:17])[CH:13]=[CH:14][CH:15]=2)[C:5]([C:19]#[N:20])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:3]=1[C:28]#[N:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:54][CH2:55][C@@H:56]([OH:59])[CH2:57][OH:58].C(N(CC)C(C)C)(C)C>CN(C=O)C.O1CCCC1.O>[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([NH:54][CH2:55][C@@H:56]([OH:59])[CH2:57][OH:58])=[O:17])[CH:13]=[CH:14][CH:15]=2)[C:5]([C:19]#[N:20])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:3]=1[C:28]#[N:29]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 6994409(2R)-3-aminopropane-1,2-diolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68597381HCID 68597381, compound

Product 1

HCID 68602346HCID 68602346, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

50 mg (0.12 mmol) of 3-({[6-amino-3,5-dicyano-4-(4-fluorophenyl)pyridin-2-yl]sulfanyl}methyl)-benzenecarboxylic acid Example 14 were initially charged in 1.2 ml of DMF. The reaction solution was cooled to 0° C. After addition of 94 mg (0.25 mmol) of HATU, the mixture was stirred at 0° C. for 20 min. 22.5 mg (0.25 mmol) of (R)-3-amino-1,2-propanediol and 32 mg (0.25 mmol) of N,N-diisopropylethylamine were added, and the reaction solution was stirred at RT overnight. Water and tetrahydrofuran were added to the reaction mixture until a clear solution had formed. The solution was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid).

Workup

  1. stirringthe reaction solution was stirred at RT overnight
  2. customhad formed
  3. customThe solution was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-9406a918b8614f73a64c458548de4198
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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